{"title":"靛红衍生亚胺的氧化扩展机制","authors":"Mariana Umba-Erazo, Rodolfo Quevedo","doi":"10.1007/s12039-024-02283-5","DOIUrl":null,"url":null,"abstract":"<div><p>Sodium borohydride induces the oxidative expansion of the imine derived from isatin and phenylethylamine to form 3-phenethylquinazoline-2,4(1<i>H</i>,3<i>H</i>)-dione. It has been proposed that this transformation occurs by <i>in situ</i> formation of hydroperoxyl anions by a reaction between sodium borohydride and atmospheric oxygen. To contribute to understanding this oxidative expansion, the reaction between the imine derived from isatin and phenylethylamine with hydrogen peroxide was studied in this work. From this reaction, 3-phenethylquinazoline-2,4(1<i>H</i>,3<i>H</i>)-dione was isolated and two by-products were identified: <i>N</i>-phenethyl-2-(3-phenethyl-ureido)-benzamide and methyl(2-(phenethylcarbamoyl)phenyl)carbamate. This article analyses the structure of these by-products and proposes a mechanism that explains the reaction.</p><h3>Graphical abstract</h3><p>It was established that the reaction of the imine derived from isatin and phenylethylamine with hydrogen peroxide produces a mixture of three compounds: 3-phenethylquinazoline-2,4(1<i>H</i>,3<i>H</i>)-dione, <i>N</i>-phenethyl-2-(3-phenethyl-ureido)-benzamide and methyl(2-(phenethylcarbamoyl)phenyl)carbamate. A reaction mechanism is proposed that explains this behaviour\n</p><div><figure><div><div><picture><source><img></source></picture></div></div></figure></div></div>","PeriodicalId":616,"journal":{"name":"Journal of Chemical Sciences","volume":null,"pages":null},"PeriodicalIF":1.7000,"publicationDate":"2024-06-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"An oxidative expansion mechanism of isatin-derived imines\",\"authors\":\"Mariana Umba-Erazo, Rodolfo Quevedo\",\"doi\":\"10.1007/s12039-024-02283-5\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>Sodium borohydride induces the oxidative expansion of the imine derived from isatin and phenylethylamine to form 3-phenethylquinazoline-2,4(1<i>H</i>,3<i>H</i>)-dione. It has been proposed that this transformation occurs by <i>in situ</i> formation of hydroperoxyl anions by a reaction between sodium borohydride and atmospheric oxygen. To contribute to understanding this oxidative expansion, the reaction between the imine derived from isatin and phenylethylamine with hydrogen peroxide was studied in this work. From this reaction, 3-phenethylquinazoline-2,4(1<i>H</i>,3<i>H</i>)-dione was isolated and two by-products were identified: <i>N</i>-phenethyl-2-(3-phenethyl-ureido)-benzamide and methyl(2-(phenethylcarbamoyl)phenyl)carbamate. This article analyses the structure of these by-products and proposes a mechanism that explains the reaction.</p><h3>Graphical abstract</h3><p>It was established that the reaction of the imine derived from isatin and phenylethylamine with hydrogen peroxide produces a mixture of three compounds: 3-phenethylquinazoline-2,4(1<i>H</i>,3<i>H</i>)-dione, <i>N</i>-phenethyl-2-(3-phenethyl-ureido)-benzamide and methyl(2-(phenethylcarbamoyl)phenyl)carbamate. A reaction mechanism is proposed that explains this behaviour\\n</p><div><figure><div><div><picture><source><img></source></picture></div></div></figure></div></div>\",\"PeriodicalId\":616,\"journal\":{\"name\":\"Journal of Chemical Sciences\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":1.7000,\"publicationDate\":\"2024-06-07\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Journal of Chemical Sciences\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://link.springer.com/article/10.1007/s12039-024-02283-5\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q3\",\"JCRName\":\"CHEMISTRY, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Chemical Sciences","FirstCategoryId":"92","ListUrlMain":"https://link.springer.com/article/10.1007/s12039-024-02283-5","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
An oxidative expansion mechanism of isatin-derived imines
Sodium borohydride induces the oxidative expansion of the imine derived from isatin and phenylethylamine to form 3-phenethylquinazoline-2,4(1H,3H)-dione. It has been proposed that this transformation occurs by in situ formation of hydroperoxyl anions by a reaction between sodium borohydride and atmospheric oxygen. To contribute to understanding this oxidative expansion, the reaction between the imine derived from isatin and phenylethylamine with hydrogen peroxide was studied in this work. From this reaction, 3-phenethylquinazoline-2,4(1H,3H)-dione was isolated and two by-products were identified: N-phenethyl-2-(3-phenethyl-ureido)-benzamide and methyl(2-(phenethylcarbamoyl)phenyl)carbamate. This article analyses the structure of these by-products and proposes a mechanism that explains the reaction.
Graphical abstract
It was established that the reaction of the imine derived from isatin and phenylethylamine with hydrogen peroxide produces a mixture of three compounds: 3-phenethylquinazoline-2,4(1H,3H)-dione, N-phenethyl-2-(3-phenethyl-ureido)-benzamide and methyl(2-(phenethylcarbamoyl)phenyl)carbamate. A reaction mechanism is proposed that explains this behaviour
期刊介绍：
Journal of Chemical Sciences is a monthly journal published by the Indian Academy of Sciences. It formed part of the original Proceedings of the Indian Academy of Sciences – Part A, started by the Nobel Laureate Prof C V Raman in 1934, that was split in 1978 into three separate journals. It was renamed as Journal of Chemical Sciences in 2004. The journal publishes original research articles and rapid communications, covering all areas of chemical sciences. A significant feature of the journal is its special issues, brought out from time to time, devoted to conference symposia/proceedings in frontier areas of the subject, held not only in India but also in other countries.
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